Hydrazine hydrate (1:1) → 1H-benzimidazole-5-carbohydrazide

HRID 1771114Notes

Reaction equation

HRID 1771114 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]2[N:13]=[CH:12][NH:11][C:10]=2[CH:14]=1)=O)C.O.[NH2:16][NH2:17]>C(O)C>[NH:11]1[C:10]2[CH:14]=[C:6]([C:4]([NH:16][NH2:17])=[O:3])[CH:7]=[CH:8][C:9]=2[N:13]=[CH:12]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 13505555Ethyl 1H-benzimidazole-6-carboxylate

Product 1

HCID 166371191H-benzimidazole-5-carbohydrazideYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

30 g of 1H-benzo[d]imidazole-6-carboxylic acid ethyl ester (0.16 mol) and 150 mL anhydrous ethyl alcohol were added to a three-necked bottle, to which 50 mL of 80% hydrazine hydrate was added. After refluxing for 4 h, the ethyl alcohol was evaporated under reduced pressure and water was added to the residual solution to isolate a solid. After sucking filtration and drying, 24.9 g solid was obtained. Yield: 88%. MS: 177 (M+1).

Workup

  1. additionwas added
  2. temperatureAfter refluxing for 4 h
  3. customthe ethyl alcohol was evaporated under reduced pressure and water
  4. additionwas added to the residual solution
  5. customto isolate a solid
  6. filtrationfiltration
  7. customdrying

Sources & evidence

ORD record
ord-26c5eb2a7c7f4048b6d9d3022db1140a
Source dataset
uspto-grants-2016_02
Patent number
US09249106B2

Reaction notes

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